Quick question - does anyone know if tax software like TurboTax handles this kind of cash income reporting well? Or is it better to use a specialized self-employment tool?

Just wanted to share my experience since I was in almost the exact same situation last year! I was doing landscaping and pet sitting for neighbors, all cash payments, and made about $3,800. You definitely need to report it all on Schedule C - there's no minimum threshold for reporting income, even if it's just $50. What really helped me was setting up a simple notebook where I wrote down every payment as soon as I got it. Date, amount, what the work was for. Super basic but it saved me when tax time came. One thing that caught me off guard was the self-employment tax. Since you made over $400, you'll owe about 15.3% of your net earnings for Social Security and Medicare on top of regular income tax. It's calculated on Schedule SE. But remember you can deduct business expenses - gas for driving to jobs, tools you bought specifically for the work, even supplies for dog sitting like leashes or treats if you provided them. The whole thing seemed overwhelming at first but once I got through it the first time, it wasn't nearly as bad as I expected. Just keep good records and you'll be fine!

Let me add a wrinkle most people don't know - if you distributed any business assets to yourself during the dissolution (like computers, furniture, etc.), that needs to be reported as a liquidating distribution on your final 1120-S. The corporation is treated as having sold these assets to you at fair market value. I completely messed this up when closing my S-corp and ended up having to amend returns. Cost me an extra $400 in accounting fees!

I went through this exact same situation with my S-corp dissolution last year and want to emphasize something that might save you some headaches - make sure you also cancel your EIN with the IRS after everything is filed and processed. Even after filing all the final returns (1120-S, Form 966, etc.) and getting state dissolution completed, I kept getting IRS notices asking about missing tax returns for subsequent years because the EIN was still active in their system. You have to specifically write to the IRS requesting EIN cancellation and include copies of your dissolution documents. Also, if you had any business bank accounts, credit cards, or merchant services tied to your EIN, close those ASAP. Some banks will report 1099s to closed business EINs which can trigger more IRS correspondence down the road. The penalty situation sucks, but as others mentioned, first-time penalty abatement is usually granted if you've been compliant in the past. Get everything filed immediately to stop the bleeding, then deal with penalty relief afterward.

Just wondering - have you looked into equity compensation restructuring? If a portion of that $1.1M is from stock options, RSUs or other equity comp, there are timing strategies that can make a huge difference. I saved nearly 6 figures last year by working with my employer to adjust my vesting schedule and exercise timing.

Given your income level, I'd strongly recommend looking into conservation easements if you own any land or are considering real estate investments. These can provide substantial tax deductions - sometimes 4-5x your investment - while preserving land for conservation purposes. Also, consider a defined benefit pension plan if you have any self-employment income or consulting work on the side. These allow much higher contributions than traditional 401ks - potentially $200k+ annually depending on your age and income. One strategy that's often overlooked is bunching deductions into alternate years. Since you're likely itemizing anyway, consider prepaying property taxes, state taxes (up to the SALT cap), and charitable donations in alternating years to maximize the benefit. Finally, if you're married, look into spousal IRA contributions and income-splitting strategies through family partnerships for any investment income. The key at your level is having multiple strategies working together rather than relying on any single approach.

Has anyone tried bunching charitable deductions? With the higher standard deduction ($29,200 for married filing jointly in 2024), we've started doing this where we donate 2-3 years worth of charitable contributions in a single year so we can itemize that year, then take the standard deduction in the off years. We're also looking into donor-advised funds where you can get the tax deduction immediately but distribute the actual charitable gifts over time. Anyone have experience with these strategies?

One strategy you might be overlooking is a backdoor Roth IRA conversion. Since your MAGI is over $146K and you can't deduct traditional IRA contributions, you could still contribute $7,000 to a non-deductible traditional IRA, then immediately convert it to a Roth IRA. This won't reduce your current tax liability, but it's tax-free growth for retirement. Also, since you mentioned having kids, make sure you're getting the full Child Tax Credit ($2,000 per child under 17). The credit phases out at higher incomes but doesn't start until $400K for married filing jointly. Another option: If your employer offers a cafeteria plan or flexible spending account beyond just healthcare, you might be able to redirect some compensation to pre-tax benefits like commuter benefits, life insurance premiums, or dependent care assistance. Finally, consider timing any major purchases or medical expenses. If you're close to the 7.5% AGI threshold for medical deductions, you might bunch medical expenses into one year to exceed the threshold.

This thread has been incredibly helpful! As someone who just moved to the US and is filing taxes for the first time, I was completely overwhelmed by all the formatting requirements. I ended up going with parentheses for all my negative numbers after reading through the official IRS publications mentioned here. What really helped was printing out a draft copy of my return and going through it line by line to make sure I was consistent throughout all the forms. One thing I learned that might help other newcomers - if you're used to different accounting standards from your home country, the US system can feel confusing at first. In my country we always use minus signs, so switching to parentheses felt weird initially. But after using them consistently, it actually makes the forms much easier to read. Thanks everyone for sharing your experiences and resources. It's reassuring to know that even small formatting questions have such a supportive community willing to help out!

This has been such a comprehensive discussion! As someone who works in tax preparation, I wanted to add a few practical points that might help future filers: If you're using tax software and still want to double-check your formatting, most programs have a "preview" or "form view" option that shows exactly how your return will look when printed or submitted. This is a great way to verify that negative numbers are formatted consistently before filing. Also, for those worried about rejection due to formatting - in my experience, the IRS automated processing systems are quite forgiving with minor formatting variations. Returns are much more likely to be flagged for mathematical errors, missing signatures, or incorrect SSNs than for using minus signs vs. parentheses. That said, following the standard conventions (parentheses for paper forms, letting software handle electronic filing) is always the safest approach. When in doubt, consistency within your own return is more important than perfect adherence to any single format standard. Great job everyone sharing resources and experiences - this kind of community support makes tax season so much less intimidating for newcomers!